On Prestige

At some point in time, we’ve all wanted things that show the world our successes or our value. Things that communicate we’re unique. That we’re worthy of respect and admiration. That we’re better than others. That our life is great.

After all, life’s a competition. It’s a cornerstone of our education from the jump… parents comparing us to other kids, teachers comparing us to other students, bosses comparing us to other employees.

We were taught to define our worth by our accomplishments. But what qualifies as an accomplishment wasn’t up to us to define. We were told what accomplishments were…

That 100 / A+ / 4.0.

That first place trophy / medal.

That name brand college we got into.

That Fortune 500 company on our resume.

That title that sounds big and important.

That 6-figure salary.

That smart, good looking person we’re dating.

That apartment in the sky.

That luxury car with more horsepower than you need.

That big rock you got from someone or for someone.

That perfect wedding.

That big house with a manicured lawn.

That picture perfect family.

There’s nothing wrong with any of these things (most are quite nice to have, actually) and prestige isn’t a bad thing to chase.

But if you are chasing prestige, are you doing it for you? And do you know why?

When the lingering voices from our parents / teachers / bosses fade away, and we’re no longer being compared to someone else, how are you defining your worth?



On Other People’s Expectations

Many of us are familiar with an existence where parents, friends, teachers, bosses, the world at large have expected us to act a certain way, to live a certain life, to abide by certain conventions/traditions, to follow the rules, to want certain things. To do otherwise would be a challenge to their beliefs, a denial of their authority, a threat to their existence.

Maybe we were seen as extensions of those parents, friends, teachers, bosses, and the world at large… extensions that represent reflections of their teachings, choices, performance, guidance, and humanity. There’s a lot at stake when someone you have tied your own value to doesn’t fall in line.

Maybe they were taught to think that way. Maybe they never thought to question what they were taught. Maybe they weren’t allowed to and if they dared there were consequences they didn’t want to bear. Maybe they never explored the alternate universe, one where they could define every. single. thing. for themselves.

I’m familiar with that world. My mom had expectations for me that I could never meet. Not only because I didn’t want to try, but because her expectations were so abstractly formed based on ideas of safety, security, convention, freedom, success, and happiness… that perhaps she wanted for her own life… but hadn’t fully grasped and understood herself.

She inherited a set of rigorously ingrained beliefs and then lived in a constant whirlwind of life coming at her where there was no time to pause, consider, and define indulgent ideas like…

… what my values are
… what makes me feel fulfilled
… what makes me happy
… what brings me joy
… what value do I want to create in this world

But we can always pause.

And we NEED to pause if we don’t know what direction we’re heading in and why.

Otherwise, what are you working so hard for?



On Dos and Don’ts

I love hot lemon water. I usually drink 3-5 glasses a day with 2-3 lemon wedges per glass. It’s usually hot, but not boiling, because that kills the good enzymes and vitamins.

My mom’s told me all my life to drink it as soon as I wake up, but I only managed the occasional cup. It wasn’t until earlier this year, when drinking hot lemon water kept coming up as a miracle morning habit on a health blog I’ve been subscribed to for years, did it become part of my morning and, eventually, all day routine.

I went to the dentist a few weeks ago and they told me how bad lemon water is, even diluted, for your teeth and enamel. I grind my teeth and have worn away a lot of the good stuff so, I’m even more at risk. If I don’t want yellower and decaying teeth in the long run, I should stop drinking the stuff (and soda water, which I’ve also grown to love). The news broke my heart for a few hours.

When I go down the list of things that are bad for me, I’m like – JESUS, JUST LET ME LIVE. Add in all the good things that I’m supposed to remember to do and life starts to look like an endless list of dos and don’ts.

But our lives already are a list of dos and don’ts. Ones that we’ve absorbed since we were born. Family, caretakers, teachers, managers, friends, partners, society, the media, etc. have all impacted our perspective of what is good and what is bad. What we should and shouldn’t do. What is important and what is not.

Over time, those dos and don’ts become part of the silent fuel that we use to power our beliefs as well as our judgments of others and ourselves. Even as we grow up and learn/believe new ideas that may contradict the old, they don’t just simply go away. It can still take time and effort to identify the old ones, make sense of them, and unroot them from the impressionable soil they were planted in.

Hot lemon water is an easy one to decide whether it stays or goes (and it may actually be bad for my teeth), but others are far more complex that I’m still working on extracting (e.g. Mistakes are acceptable and you’re not less smart/valuable/worthy for having committed them). Some are still to be identified, which is a little terrifying.

All that to say, whether it’s hot lemon water you’re trying to make the call on or whether your “silly” dreams are worth chasing, your life is yours to design however the hell you want – all experts be damned.


On What We’re Working For

What are you working for?


Is it for the value you’re creating?  

The purpose you’re serving?  

The stability you’re experiencing?

The results you’re achieving?

The recognition you’re receiving?  

The money you’re earning?  

The prestige you’re feeling?  

The validation you’re getting?  

Any reason is viable as long as we know what it is and are at peace with it.

If not, it’s an opportunity to evaluate why we’re in the situation we’re in and if it’s still worth it.

It’s hard to get off the track you’re on. It’s usually easier to follow the forward momentum and rinse/repeat.

But the flip side is that sometimes your life depends on you getting off that track. To make a conscious choice to stop the train and change course in a direction that makes you feel alive again.



On A Job Just Being A Job

Sometimes a job is just a job. You have it so you can pay the bills, support you/your family, save for something big, get out of debt (or into it), have stability, or serve some other purpose.

A job being a job is totally fine and admirable, if you’re clear on why you’re doing it.

If you don’t, it’s easy to fall into the trap of feeling like you’re not fulfilled, you’re not creating value, or you’re stuck.

But it’s ok to want more from your work. It’s ok to want to feel fulfilled. It’s ok to want to create value. These things give life meaning and make us feel like we’ve done something worth our while.

On the flip side, if you want all those things from your work and aren’t getting it, you may start to feel like you’ll never find those things, you’re expecting too much, and maybe a job is just a job.

On either side, a job is not going to fulfill all the parts of you that need fulfilling and give you the full sense of purpose that you want to feel. And neither will a relationship, or a new home, or a puppy, or a child. They’re component parts, but it’s way too much to ask of any one thing or person.

But you can start by defining what your purpose is, what it means to you to be fulfilled, and what creating value looks like to you. Then you can look at the component parts and break down what you want to get out of each.

If you start there, you’ll be far better equipped to find the work, the relationships, and the other things you need to piece your full life together. And though life doesn’t guarantee you’ll find them all, at least you’ll know what you’re looking for.



On Asking Why

We ask why when we don’t understand something. (After typing that sentence I looked up the meaning of why, because I don’t think I’ve ever done that. Oxford said, “For what reason or purpose.”)

When asked it’s usually an innocent question prompted by genuine curiosity, but it’s not always taken that way.

Sometimes it’s viewed as a challenge. Or a questioning of authority. Or an annoyance. Or disloyalty. Or a dig. As an incessant question asker, especially of why, I can vouch for all of these reactions.

As a kid, I was yelled at for being a pest and for questioning commands. As an employee, I’ve gotten feedback from multiple managers at various jobs that I needed to not challenge the direction I was given and just follow orders. As a friend, my questions made others feel like I wasn’t on their side. As a partner, I’ve been told that I wasn’t being supportive and understanding.  

And this whole time, I’ve felt wildly misunderstood.

I live for asking why. It’s an honest passion and a fundamental motivation of my existence to understand why things happen, why people do the things they do, why people are the way they are. I light up when there’s a topic I don’t understand and I have an opportunity to ask someone about it. 

But in my early twenties I realized I wasn’t asking myself why enough. Why did I make the choices I made? Why did I react the way I did? Why were my passions my passions? Why am I motivated by certain things? Why did I sometimes respond to questions of why with the same defensiveness as I’ve received?

(On that last one, it was usually because I didn’t know the answer and that was extremely uncomfortable. It still is.)

It’s not the best feeling to not know things in front of our family, coworkers, friends, and partners. But the scariest whys are the ones we don’t know about ourselves. Because if you don’t know, who would?

But figuring out what to do with your life is a self-directed path that includes asking yourself a ton of hard questions that often include the word why. Sometimes it may seem like it’s derailing you from your end goal, but the path isn’t straight and going down a why tunnel may be necessary to figure out what your end goal even is.

The journey may not be rainbows and sunshine all the time, actually it can be pretty painful, but if we can look at asking why as an opportunity to learn about ourselves and start getting comfortable facing that question, we may find that most of the answers we’re looking for sit at the end of that tunnel.

So, jump in.



On Doing Things You Hate 

I haaaaaaaate running. The idea of it makes me cringe. It sounds like self-inflicted torture on your calves, back, stomach, lungs, etc. People that love to run are aliens to me. The last time I ran I remember thinking I’ll never do this again and it might’ve been for a mile, max.

The one thing I do like about running is the idea that you can walk out the front door and get going. But if you hate the act itself, that benefit is pretty useless.

But I’ve been feeling fat and stagnant… full on winter hibernation in effect. So, when the boyfriend asked if I wanted to join for a run last Sunday (I’ve never gone running with him and haven’t “run” for about 1.5 years), it seemed like a simple way to not feel like a total waste of life.

But after I said yes, I immediately started bargaining. I suggested parameters like 1 mile max and I’d Lyft home if he wanted to continue. I didn’t know if I had the right clothing for running in 40 degree weather so, I wasn’t sure if I should go. I would slow him down and he wouldn’t get his exercise in so it really didn’t make sense for me to go. Yadda yadda yadda.

He had a solution for all my concerns so, I ended up running for the first time in a year and a half. I was nervous… already thinking about when I’d have to turn back and how I was gonna get home. But my very patient partner told me to take it slow, find my rhythm, and breathe slowly.

And shockingly, that advice worked really well, especially the find-your-rhythm-bit. I took small steps and kept to the sweet spot of rhythm that didn’t tire me out and pretty quickly we made it to the river (about 1.6 miles away). That was truly as far as I thought I could go, but he convinced me to keep going with an option to walk a bit if I needed. I ended up walking for 3/4 of a mile, maybe a full mile, but either way I’d gone 3.8 miles when we called it, which was totally insane to me.

There’s no way in hell I would’ve believed I could run (most of) 3.8 miles when we started or even halfway through. I was so exhausted, but so damn happy… one of those small but precious moments when you realize you’re body’s pretty damn amazing and you really don’t know what you can do till you try. (I do hate when thoughts echo cheesy motivational quotes.)

Sometimes we need people to push us and show us how it’s done to make it feel less daunting (keep those people around). Sometimes we just need to take that first step out the door regardless of whether we have the right equipment or whether we know exactly what we’re doing. Sometimes we need to stop telling ourselves we can’t when we haven’t even tried.

If for no other reason than to simply show ourselves we can do the damn thing and challenge our beliefs about ourselves.

In the grand scheme of things, doing one run doesn’t mean much, but if I can string a few of these moments together over a consistent period, however mundane, I can only imagine what that can do for my outlook on what’s possible in this life of mine.

I don’t think running’s gonna be my thing, but there’s a crack of light coming through the running door that wasn’t there before and I’m not mad about it.



On Job Titles

Titles can be elevating. They can give us a sense of worth and status. They can make us feel good when we say, “I’m the ___ at ___,” when people ask what we do.

Titles can be constraining. They can be less than what we think we deserve and inaccurate at depicting our full value. We may not want to use it when people ask what we do.

Titles can carry a ton of weight in certain crowds, immediately prompting more focus and interest from the listener, who suddenly thinks we’re way cooler now that we’ve said a few words that give us more value to them.

Titles don’t mean a thing in certain crowds, where people couldn’t give two shits whether we’re a dishwasher or a Head of blah blah blah. They want to know where we’re from and what we’re into.

Titles can be a quick way to evaluate success and how well we’re doing in life. Our moms may tell all her friends about her baby’s great job at___ leading ___ even though she has no idea what we do. Meanwhile, we dream about quitting everyday to go travel the world.

Titles can lead people to think we’re not doing as well as they think we should based on a standard that doesn’t actually exist. “Didn’t she go to a good school? I thought she’d be ___ by now. What happened?” Yet we’re the healthiest we’ve ever been, living the best life we ever have and are the happiest motherfuckers out there.

Titles are supposed to serve as short descriptions of responsibility and seniority. They’re supposed to be useful in identifying career paths, skillsets and progression.

Instead they’re often intertwined with identity. It starts to be an easy way to introduce ourselves to people. The Headline on LinkedIn, the bios on Insta/FB/Medium, the nametags at events, etc. After a while, we can start to feel lost without them.

But there may be many moments when we lose them… layoff, transition, retirement, taking a break, making a major life change, etc. Or when life happens and we take on new ones or old ones evolve.

So, do you know who are you with and without them? What defines you if it’s not your title? What do you do for yourself, the people you love, the causes that matter to you, the world?

The clearer those answers are, the easier it’ll be to face all the social and societal pressure that will constantly challenge what we believe. Parents, teachers, managers, recruiters, friends, family, partners may all mean well, but they’re not responsible for what you do with this life and they don’t have to face the reckoning in those silent moments when it’s just you, your inner voice and the life you’ve lived.

Instead of letting someone else define your worth and assign your value, figure out what yours is. Know it to the core. Live it fully. Remind yourself regularly. Be skeptical of anything that makes you doubt your clarity. Factor in your growth. Evolve as needed. Reaffirm your conviction. Repeat.



On What Success Looks Like

I used to think there was a specialty/industry/profession (aka “IT”) that I was meant to be doing. I just had to find IT (“I’m a doctor! I’m a consultant! or I’m a businesswoman!”), work hard, and all the other pieces would fall into place.

I’d have a big title at a big company with a big salary doing a thing that everyone would be impressed with and maybe, even a little jealous of.

I started imagining myself in power suits before I ever put a suit on and realized how uncomfortable they were.

I remember thinking, “I should be CEO of a Fortune 500” without understanding what a CEO did or what the Fortune 500 was.

I pictured myself on the covers of magazines and being interviewed about some awesome thing I just did b/c I was fucking amazing at whatever IT was.

Luckily, I found my first IT at age 10. I knew I wanted to work in sports after going to my first Knicks game and decided soon after that I was going to be Commissioner of the NBA one day. I didn’t waver much from that for the next dozen years and everything work-related I did from there on out was driven by that goal. (And maybe… a penthouse in Manhattan and a house in the mountains with 2–3 perfect kids and a yellow lab named Bailey.)

When I got to the NBA at 22, I thought I’d made it… the dream was coming together, I was on the ladder I needed to climb and I just had to put one foot in front of the other. So simple.

But jobs and corporations are messy and political and bureaucratic and 2 years into it, I had to admit to myself.. I don’t think I want to be Commissioner of the NBA anymore.

I got IT wrong, the future seemed uncertain, I beat myself up for not making the right decision, I thought I was a failure, etc, etc.

But after a few months off, a cross country roadtrip, many late nights bartending and lots of alone time reading in Central Park, I pulled it together enough to revisit the drawing board and try to figure IT out again. I thought, I got it wrong for the last 12 years of my life, but now I was more mature, more experienced and less naive than my 10–22 year old self so, this time I’d get it right and I wouldn’t have to go through this shit again.

I fount my next IT — Head of Marketing for ESPN. A few years later… same shit.

Then the next IT — I’m gonna work in food and start my own bar/restaurant.  Again… same shit.

I was great at (or delusional in) overshooting and jumping to the end result I thought I wanted to achieve, but was terrible at getting super clear on the WHY and whether I’d want to take all the steps to get there.

In my defense, I thought I had sorted the WHY. But it was the lazy version, which netted answers like ” b/c I love basketball!” or “b/c I want to focus on the consumer,” or “b/c I get to create/attend these incredible events that most people only dream of,” or “b/c I’m obsessed with restaurants!”

Problem is, not going deep and getting super clear on the WHY usually made me feel like I had to start from scratch each time I lost interest. Sometimes it took a few months to realize that and other times it took a few years, but eventually the lazy WHY couldn’t hold up b/c it wasn’t solid enough to support the path I chose.

After a bunch of different jobs at a bunch of different companies in a variety of industries, revisiting the drawing board many times over, starting my own business and taking multiple breaks to “find myself”… it’s now clear that finding an IT isn’t enough. Seems so obvious now, but it took a few turns for that to sink in.

That’s not to say I didn’t learn a ton with each choice I made and I really don’t regret any of the decisions made, but the process of choosing a path, committing to it all in, starting to see the cracks, reconciling conflicting feelings between what I felt deep down with what I thought my goals were, finally admitting that I had to make a(nother) major life change, then actually going through with it, was fucking brutal.

So, instead, here’s what I do now. What sustainably sets me up for fulfillment in the long run is understanding:

  1. What I want to accomplish in life long-term
  2. What I value in work, in relationships and in my home/community
  3. What my day to day environment and interactions entail

Answering these gives me a set of north stars regardless of what job I have, what circumstances I’m in, how much money I make, or who I’m surrounded by and they are entirely dictated by my own WHYs for being.

I may not have them all right now and they may evolve later on, but at this moment they are the fundamental hopes, dreams and desires for what I want my life to look like. Together, they add up to my definition of success and what a good life looks like and I use them as the filters through which I make the big decisions.

The exercise seems simple, but the process isn’t always easy b/c it requires digging a few levels deep into your WHYs and that can be uncomfortable. As a rule of thumb, 3–5 follow up WHY?s after the first answer you come up with is a good measure to get into the real, real stuff.

After that, staying focused on what you come up with isn’t always easy or popular. Our parents, friends, society, schools, the media are all responsible for creating and propagating set definitions of success and what we should be doing with our lives. We’ve all been influenced by it in some way, big or small.

It’s definitely messed with my head many times over and it still does sometimes. But each time that happens — a friend says something that challenges my choices or something triggers a doubt in my head on whether I’m doing the right thing — I have to remind myself what my own success definition is. And I have to do it emphatically and confidently… 100% conviction

What I’m fighting against aren’t just my own doubts in the moment, but the entrenched societal norms that have been working their way through my brain since I was born. Those norms had evangelists in the form of my mom, relatives, guidance counselors, professors, bosses and over time they even convinced some of my friends, significant others and coworkers to join the cause.

It’s incredibly easy for others to tell me all the things I shouldn’t be doing b/c they don’t have to live with the choices. In addition, the more criticism I’ve gotten, the more I see that it’s less about me and more about them and their uncomfortable feelings that are triggered… whether it scares them, makes them jealous, threatens their beliefs, makes them question their choices, etc. All that makes it easier to ignore the noise, remember that we’re all trying to figure our shit out and no one knows any better than anyone else. And certainly not when it comes to how other people should be living their lives and what success should look like.

So, do you know what your success definition is? If you take a stab using the framework above, let me know if I can help.


On Being “Happy”

When I was a kid, I remember telling me mom that all I cared about in life was being happy. She responded that there was more to life than being happy and I thought she was insane. Back then, it seemed like my mom and I disagreed on 95% of life so, I figured that she just didn’t understand the purpose of living as well as I did. I was 15.

Now in my 30s, I still think she’s a bit nutty at times, but I do agree that there’s more to life than being happy. It’s one thing to consider, but not the thing.

Let me define happy/happiness in this context so no one gets upset when I say happiness is not the most helpful thing to chase.

Happy means feeling or showing pleasure or contentment. And happiness is the quality or state of being happy.

I don’t use happiness as a filter for making important decisions anymore b/c I’ve found it to be unreliable. Happy is a feeling and happiness is a state, which can come and go, moment to moment, situation to situation. And that’s just not solid enough to base important decisions on.

What made me happy yesterday may not make me happy today, or in a month, or in a year. I’m affected by the weather, by people around me, by culture, by where I live, by my baggage, by my/others’ expectations and whether I’m happy just scratches the surface of all my shit buried underneath.

In the first 10+ years following that convo with my mom, I stayed the course and asked “Am I happy?” or “What makes me happy?” to sort my life. From tiny choices… should I go out tonight even if I have to be at work at 8am?… to massive ones… should I end this relationship even though he’s such a good person and checks so many boxes?

But once I got to my mid twenties and really started thinking about what I wanted in life, being happy wasn’t as helpful of a guide as it used to be. I made changes and adjusted course based on my level of happiness, but it didn’t always get me to a better place in the long run.

When I left what once was my dream job at the NBA, I had been unhappy for months. I hated going to work every morning and didn’t find value in what I was doing anymore. But I also didn’t know what else I wanted to do so, I didn’t try interviewing for other jobs. I probably indulged the unhappy place when I shouldn’t have, but it reached a level I couldn’t stand anymore so, I quit (without a plan).

I ended up bartending then drove around the country for two months, the latter of which was one of the best things I’ve done in my entire life. But when I got back home, I still had no idea what I wanted to do. Within a few weeks, I was back to the same rut and feeling like the gif at the top.

I realized I hadn’t dug into the problem deep enough to know what I needed to solve for and the “Am I happy?” filter was an easy way out of a situation I didn’t like. The road trip was an amazing break and I 100% did not regret going, but it only delayed solving the I’m-not-happy problem.

It took me another two months before I got my shit together. But eventually, I sorted that I wanted to…

  • Stay in NYC
  • Work for someone I looked up to and could learn from
  • Grow my skills in brand marketing
  • Stay in sports, but be closer to the sport itself and not just selling the sport
  • Earn more money
  • Have better work/life balance

If I got that, it’d probably make me happy, but more importantly I’d be solid. I’d feel good about the direction I was moving in life. After two months of evaluating what I wanted, I found a few more useful goals to chase other than happiness; useful b/c they were actually tangible. Happiness is subjective and even if I got all those things I’d still have unhappy days. But whether your life good is something you can evaluate in more black and white terms based on how you’ve defined it. You just gotta define it.

From then on I started to consider my choices more and more through the lens of good instead of happy. On those inevitably shitty days where I was in a crappy place for whatever reason, I’d try to switch gears and think about “Am I good with my overall situation right now?” and “Do I have/Am I doing the things that make me feel solid?” instead.

I wasn’t always successful b/c the happy trap is strong, but when I did, I was able to answer those questions far more objectively, and often with a simple yes or no. If it was a yes, then I knew I was actually fine and just running higher on the emotions that day. If it was a no, then I needed to consider why I wasn’t in a good place and if my goals were still valid.

I’ve had to repeat the process of defining “good” a bunch more times since b/c I’ve changed a lot since 24 and what I wanted/what made me feel solid changed with that. It usually sucked b/c I often had to do it after a period of feeling stuck, overwhelmed, sad, angry, broken… and yes, unhappy. But doing so was the only way I knew to get out of that shitty place.

“Am I happy?” definitely still has a place in the life toolbox. I use it as a temp check to see how I’m feeling on the regular so I know how my emotional meter is trending over time. If I’m consistently trending downwards, then that’s another way I know I need to reevaluate what’s happening in my world and if I’m good or not.

Yes, this is partly an exercise in semantics and if it works for you to use the word happy to define how solid you feel in the world, then by all means. But the distinction between “happy” and “good” has helped me better understand what’s actually going on in my head and make better decisions.

Happy is an emotion and our emotions are not based on reason so, breaking out the parts that I can evaluate rationally from the ones that I can’t give me a higher percentage shot at making the best decision b/c it’s not just based on a temporary feeling. It’s based on the specific things I’ve identified as being good for my life.

Being happy can be elusive b/c it’s amorphous and fluid. But being good with where you are/what you’re doing with your life right now… That’s 100% definable.